Synthesis of the tetrasaccharide core region of antigenic lipo-oligosaccharides characteristic of Mycobacterium kansasii

Carbohydr Res. 1988 Apr 15;175(2):241-8. doi: 10.1016/0008-6215(88)84146-6.

Abstract

The oligosaccharide core region, beta-D-Glcp-(1----3)-beta-D-Glcp-(1----4)-alpha-D-Glcp- 1----1)-alpha-D-Glcp (1), of the lipo-oligosaccharide-type antigens isolated from M. kansasii has been synthesised from 2,3,2',3',4',6'-hexa-O-benzyl-6-O-(1-phenylethyl)-alpha, alpha-trehalose (4). Compound 4 was obtained by LiAlH4-AlCl3-type hydrogenolysis of 2,3,2',3',4',6'-hexa-O-benzyl-4,6-O-(S)-(1-phenylethylidene)-alpha , alpha-trehalose. The beta-laminaribiosyl part of the molecule was built-up by sequential glycosylation steps using 2,4,6-tri-O-acetyl-3-O-allyl-alpha-D-glucopyranosyl bromide in the presence of HgBr2 and methyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranoside promoted by methyl triflate. The complete a priori 13C-n.m.r. spectrum assignment of 1 was achieved by applying 2D methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Indicators and Reagents
  • Lipopolysaccharides / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Mycobacterium / immunology*
  • Oligosaccharides / chemical synthesis*
  • Optical Rotation

Substances

  • Indicators and Reagents
  • Lipopolysaccharides
  • Oligosaccharides
  • lipid-linked oligosaccharides